Homeless families with children have been increasing in numbers over the past 2 decades. Chronic homelessness creates economic strains within communities and barriers for homeless people to become self-sufficient. Previous research has been conducted on homeless individuals. However, little literature exists regarding characteristics of women with children who were formerly homeless but are now stably housed. Therefore, this study investigated themes and characteristics of 10 formerly homeless women who are now stably housed after living in transitional housing. Participants were observed and interviewed using a naturalistic case study design. Childhood histories, perceptions of relationships, affiliations, stress factors, life attitudes, and beliefs of the participants were documented. Content analysis was used to extract themes from the data. Findings from this research revealed that childhood trauma was a precipitating factor to adult decision making and relationship choices in adulthood. Positive changes reported by the women included enhanced self-esteem, motivation, and autonomy. Social change implications of this study may include prevention of chronic homelessness by the provision of social services supports in conjunction with transitional housing.